Sodium Dithionite → Vercirnon

HRID 2409113Notes

Reaction equation

HRID 2409113 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:38])C=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22](=[O:29])[C:23]2[CH:24]=[CH:25][N+:26]([O-:38])=[CH:27][CH:28]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 98239374-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide

Product 1

HCID 10343454VercirnonYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide (191 g) in dichloromethane (3000 mL) was added m-chloroperbenzoic acid (65%, 146 g) at 0° C., and the mixture was stirred for 30 min. The mixture was warmed to room temperature and stirred for 16 hr. The mixture was cooled to 0° C., 10% aqueous sodium dithionite solution (630 mL) was added, and the mixture was stirred for 30 min and extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (500 mL) and saturated brine (500 mL). The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and purified by silica gel column chromatography (NH, chloroform) to give the object 4-tert-butyl-N-[4-chloro-2-(1-oxidoisonicotinoyl)phenyl]benzenesulfonamide (181 g, pale-yellow solid).

Workup

  1. stirringstirred for 16 hr
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringthe mixture was stirred for 30 min
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (500 mL) and saturated brine (500 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. custompurified by silica gel column chromatography (NH, chloroform)

Sources & evidence

ORD record
ord-04f9b1dcbc2747898d40be7422e7315d
Source dataset
uspto-grants-2014_08
Patent number
US08815887B2

Reaction notes

Loading…